반응 #67028

반응 방정식

aminoguanidine hydrochloride

1-cyclopropyl-4-isothiocyanato naphthalene

diisopropylethylamine

→

5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol

수율 50.6%

용매

DMF

반응 조건

후처리

1. 1
   기타The solvent was removed under reduced pressure, toluene
2. 2
   workup.ADDITIONadded
3. 3
   기타the solvent was evaporated again
4. 4
   workup.ADDITIONSodium hydroxide solution (2M, 30 mL) was added
5. 5
   온도the reaction mixture heated at 50° C. for 60 hours
6. 6
   여과The reaction mixture was filtered
7. 7
   여과The mixture was re-filtered
8. 8
   기타the solvent removed under reduced pressure
9. 9
   기타The residue was purified by silica gel chromatography

실험 절차

A mixture of aminoguanidine hydrochloride (3.18 g, 29 mmol), 1-cyclopropyl-4-isothiocyanato naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50° C. for 15 hours. The solvent was removed under reduced pressure, toluene added, and the solvent was evaporated again. Sodium hydroxide solution (2M, 30 mL) was added and the reaction mixture heated at 50° C. for 60 hours. The reaction mixture was filtered and the filtrate neutralized with aqueous HCl (2M). The mixture was re-filtered and the solvent removed under reduced pressure. The residue was purified by silica gel chromatography to yield 5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol (2.0 g, 49%).

출처